Structure and isomerization of α-phenylcinnamic acid stereoisomers - Reaction pathway and transition-state structure by semiempirical methods

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Abstract

The isomerization reaction of E- and Z-α-phenylcinnamic acid molecules was studied at the level of semiempirical quantum chemical methods (MNDO, AM1 and PM3). Calculations revealed that Z-α-phenylcinnamic acid is slightly more stable than the E isomer. The activation enthalpy for isomerization and the transition-state structure were also determined. The difference in the acidities of the two stereoisomers of α-phenylcinnamic acid and cinnamic acid (this is the basis of their separation experimentally) was rationalized by computing the dipole moments of the ions.

Original languageEnglish
Pages (from-to)189-192
Number of pages4
JournalJournal of Molecular Structure: THEOCHEM
Volume391
Issue number1-2
Publication statusPublished - Feb 28 1997

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Stereoisomerism
Isomerization
isomerization
acids
Acids
Dipole moment
Acidity
Isomers
Enthalpy
Chemical activation
Ions
Molecules
acidity
dipole moments
isomers
enthalpy
activation
molecules
ions
cinnamic acid

Keywords

  • E- and Z-phenylcinnamic acid
  • Isomerization pathway
  • PK
  • Semiempirical method
  • Transition-state structure

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

Cite this

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abstract = "The isomerization reaction of E- and Z-α-phenylcinnamic acid molecules was studied at the level of semiempirical quantum chemical methods (MNDO, AM1 and PM3). Calculations revealed that Z-α-phenylcinnamic acid is slightly more stable than the E isomer. The activation enthalpy for isomerization and the transition-state structure were also determined. The difference in the acidities of the two stereoisomers of α-phenylcinnamic acid and cinnamic acid (this is the basis of their separation experimentally) was rationalized by computing the dipole moments of the ions.",
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T1 - Structure and isomerization of α-phenylcinnamic acid stereoisomers - Reaction pathway and transition-state structure by semiempirical methods

AU - Tasi, G.

AU - Pálinkó, I.

AU - Körtvélyesi, T.

AU - Nyerges, L.

PY - 1997/2/28

Y1 - 1997/2/28

N2 - The isomerization reaction of E- and Z-α-phenylcinnamic acid molecules was studied at the level of semiempirical quantum chemical methods (MNDO, AM1 and PM3). Calculations revealed that Z-α-phenylcinnamic acid is slightly more stable than the E isomer. The activation enthalpy for isomerization and the transition-state structure were also determined. The difference in the acidities of the two stereoisomers of α-phenylcinnamic acid and cinnamic acid (this is the basis of their separation experimentally) was rationalized by computing the dipole moments of the ions.

AB - The isomerization reaction of E- and Z-α-phenylcinnamic acid molecules was studied at the level of semiempirical quantum chemical methods (MNDO, AM1 and PM3). Calculations revealed that Z-α-phenylcinnamic acid is slightly more stable than the E isomer. The activation enthalpy for isomerization and the transition-state structure were also determined. The difference in the acidities of the two stereoisomers of α-phenylcinnamic acid and cinnamic acid (this is the basis of their separation experimentally) was rationalized by computing the dipole moments of the ions.

KW - E- and Z-phenylcinnamic acid

KW - Isomerization pathway

KW - PK

KW - Semiempirical method

KW - Transition-state structure

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